A. A. Bredikhin, Z. A. Bredikhina, A. V. Kurenkov
Oct 15, 2017
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Based on the features of its crystallization, racemic 3-(2,3-dimethylphenoxy)propane-1,2-diol 2 , the synthetic precursor of the chiral drug xibenolol 1 , was resolved into pure enantiomers by the direct method of entrainment. The enantiomers of diol 2 through a Mitsunobu reaction were converted into the nonracemic 1,2-epoxy-3-(2,3-dimethylphenoxy)propanes ( S )- and ( R )- 3 , and then into the xibenolol enantiomers. Single crystals of (+)- and (−)- 1 ·HCl were studied by X-ray diffraction. On the basis of the Flack parameter, the absolute ( R )- and ( S )-configurations were assigned to these compounds and to the other intermediate chiral substances.